4-Nitro-1H-indole → HCID 57850033, compound

HRID 736593Notes

Reaction equation

HRID 736593 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11]C=C2[C:5]=1[CH:6]=[CH:7]N2)([O-:3])=[O:2].[CH3:13][N:14]([CH:16]=[O:17])C.C[OH:19]>>[CH:11]([C:12]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:13]=1[NH:14][CH:16]=[O:17])=[O:19]

Participants

3

Reactant 2

HCID 1457664-Nitro-1H-indoleHCID 21901440N,N-dimethylformamide methanol

Product 1

HCID 57850033HCID 57850033, compoundYield 55%

Procedure

A stirred solution of 4-nitro-1H-indole (4a, 93.8 g, 0.56 mol) in DMF-MeOH (1:2, 2.7 L) cooled in a dry ice-acetone bath was bubbled with ozone (generated from oxygen gas, 22 g/m3, flow rate 500 L/hr, ozone generator: Tokyo Keiso, 11 g/hr) for 3.5 h. The mixture was kept cool in the dry ice-acetone bath for 1 h without stirring. The precipitate generated was filtered and washed with H2O to give N-(2-formyl-3-nitrophenyl)-formamide (5a, 62.0 g, 55%), 1H NMR (270 MHz) δ (DMSO-d6) 7.82 (t, J=7.9 Hz, 1H), 7.91 (d, J=7.9 Hz, 1H), 8.15 (m, 1H), 8.37 (br, 1H), 10.07 (s, 1H), 10.71 (br, 1H); MS (EI) m/z 194 (M+).

Workup

  1. customwas bubbled with ozone (generated from oxygen gas, 22 g/m3, flow rate 500 L/hr, ozone generator: Tokyo Keiso, 11 g/hr) for 3.5 h
  2. temperatureThe mixture was kept cool in the dry ice-acetone bath for 1 h
  3. filtrationThe precipitate generated was filtered
  4. washwashed with H2O

Sources & evidence

ORD record
ord-b4c1c173edba42e59de4a288bb265043
Source dataset
uspto-grants-2009_09
Patent number
US07595400B2

Reaction notes

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